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Check availability on Islamorada Luxury Hotels

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Islamorada luxury hotels

Balcony
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1278)
"Fabulous waterfront, activities, and dining as well as the staff. "
Canada
David
The price is ฿12,418
฿16,247 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cheeca Lodge & Spa
Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1267)
"Friendly staff and beautiful property !"
United States
ron
The price is ฿7,332
฿10,315 total
includes taxes & fees
4 Jan - 5 Jan 2026
Amara Cay Resort
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Drop Anchor

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1000)
"Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing! "
United States
Laura
The price is ฿4,373
฿6,009 total
includes taxes & fees
4 Jan - 5 Jan 2026
Drop Anchor
In-room safe, individually decorated, individually furnished
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (119)
"Beautiful place to stay"
United States
Jonathan
The price is ฿7,910
฿10,965 total
includes taxes & fees
4 Jan - 5 Jan 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
View from property
Creekside Inn

Creekside Inn

Creekside Inn
2.5 star property
Tavernier
8.0 out of 10, Very good, (1000)
"The room was nice, but walking out to the pier from door was excellent "
United States
Anthony
The price is ฿4,734
฿5,326 total
includes taxes & fees
5 Jan - 6 Jan 2026
Creekside Inn
Private beach, white sand, sun-loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1602)
"The entire resort was wonderful."
Canada
Mat
The price is ฿5,884
฿8,370 total
includes taxes & fees
6 Jan - 7 Jan 2026
Chesapeake Beach Resort
Property grounds
Conch On Inn Motel

Conch On Inn Motel

Conch On Inn Motel
2.0 star property
Indian Waterways
7.6 out of 10, Good, (488)
"Overall great experience & owners were great. Only thing I would offer up is could use some new mattresses but everything else was more than expected! Would (or shouldsay will) stay again someday"
United States
Anonymous traveller
Conch On Inn Motel
Beach nearby, white sand, sun-loungers, beach umbrellas
Casa Morada

Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (415)
"always a pleasant stay."
United States
robert
The price is ฿11,275
฿14,587 total
includes taxes & fees
24 Dec - 25 Dec
Casa Morada
Exterior
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1010)
"We enjoyed are stay at Fisher Inn, room was clean and updated. The paddle board use was a nice perk! "
United States
Magaly
The price is ฿5,040
฿6,685 total
includes taxes & fees
5 Jan - 6 Jan 2026
Fisher Inn Resort & Marina
Exterior
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1002)
"The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful"
United States
Theresa
The price is ฿13,719
฿17,535 total
includes taxes & fees
9 Jan - 10 Jan 2026
Islander Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Islamorada Hotel Reviews

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Clean rooms! Great resort , fun activities , very nice and quiet area , made my anniversary with my girlfriend very special! "
Nicolas 1-night trip
Posted 2 days ago
Amara Cay Resort

Frequently asked questions

Are you looking for a luxury hotel for your stay in Islamorada?
Known for its ocean views and sunsets, Islamorada also has some interesting things to see and do including Everglades National Park, so you may want to take in the local sights during your visit.
What's the best luxury place to stay in Islamorada?
Cheeca Lodge & Spa is a luxury resort with a private beach and 3 restaurants, and it's a popular choice for Expedia travellers looking for an elegant place to stay.
When can I expect good weather in Islamorada?
Planning for the weather is an important factor for making your trip to Islamorada a success, especially when you're splurging. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.
What's there to see and do in Islamorada?
Experience all that Islamorada has to offer when you visit Everglades National Park, Florida Keys Brewing Co. and Bud n' Mary's Dive Center. If you have a bit of extra time while you're in the area, you might want to check out Islamorada County Park and Founders Park.